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Triethylamine → 1-ethyl-1-methylpropyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate

HRID 2061232
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2061232
[CH2:1]([C:3]([CH3:14])([O:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])[CH2:4][CH3:5])[CH3:2].[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl.CN(C)C=O>[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:31][CH2:32][N:33]([C:11](=[O:13])[CH2:10][NH:9][C:7](=[O:8])[O:6][C:3]([CH2:1][CH3:2])([CH3:14])[CH2:4][CH3:5])[CH2:34][CH2:35]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1
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Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 85792234{[(1-Ethyl-1-methylpropoxy)carbonyl]amino}acetic acid

Produkt 1

HCID 59853919
1-ethyl-1-methylpropyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

284 mg (1.40 mmol) of {[(1-ethyl-1-methylpropoxy)carbonyl]-amino}-acetic acid, 320 mg (1.17 mmol) of 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-piperidine and 322 mg (1.68 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride were dissolved in a mixed solvent of 15 ml of dichloromethane and 5 ml of dimethylformamide. 0.23 ml (1.68 mmol) of triethylamine and 14.7 mg (0.12 mmol) of dimethylaminopyridine were added to the obtained solution, and they were stirred at room temperature overnight. After the concentration under reduced pressure, ethyl acetate was added to the reaction mixture. The resultant mixture was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by the silica gel chromatography (hexane:dichloromethane=95:5 to 2:3) to obtain the title compound.

Aufarbeitung

  1. concentrationAfter the concentration under reduced pressure, ethyl acetate
  2. additionwas added to the reaction mixture
  3. washThe resultant mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by the silica gel chromatography (hexane:dichloromethane=95:5 to 2:3)

Quellen und Nachweise

ORD-Eintrag
ord-ec38d52018ae45998077107d6402f576
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08278329B2

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